Trifluoroacetic acid → HCID 178511551, compound

HRID 1819458Notes

Reaction equation

HRID 1819458 reaction equation
C(OC(=O)[NH:7][CH:8]1[CH2:13][CH2:12][CH:11]([CH2:14][NH:15][C:16]2[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][N:19]=[C:18]([NH:25][CH2:26][C:27](=[O:33])[N:28]3[CH2:32][CH2:31][CH2:30][CH2:29]3)[N:17]=2)[CH2:10][CH2:9]1)(C)(C)C.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[NH2:7][C@H:8]1[CH2:9][CH2:10][C@H:11]([CH2:14][NH:15][C:16]2[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][N:19]=[C:18]([NH:25][CH2:26][C:27](=[O:33])[N:28]3[CH2:32][CH2:31][CH2:30][CH2:29]3)[N:17]=2)[CH2:12][CH2:13]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 59845673HCID 59845673, compound

Product 1

HCID 178511551HCID 178511551, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(4-{[5-Nitro-2-(2-oxo-2-pyrrolidin-1-yl-ethylamino)-pyrimidin-4-ylamino]-methyl}-cyclohexyl)-carbamic acid tert-butyl ester (19 mg, 0.04 mmol) was dissolved in CH2Cl2 (5 mL) and TFA (1 mL) was added. The reaction mixture was stirred at room temperature for 1 h. The solution was treated with saturated NaHCO3 and the organic phase was separated. The aqueous phase was extracted with CH2Cl2 and the combined organic phase was dried over Na2SO4 and concentrated. The resulting residue was purified by silica gel prep TLC using 10:1:0.3 CH2Cl2:MeOH:Et3N as an eluant to afford 13 mg of the title compound as a light yellow solid (83%), m/z 376.3 [M−1]+.

Workup

  1. customthe organic phase was separated
  2. extractionThe aqueous phase was extracted with CH2Cl2
  3. dry with materialthe combined organic phase was dried over Na2SO4
  4. concentrationconcentrated
  5. customThe resulting residue was purified by silica gel prep TLC

Sources & evidence

ORD record
ord-c926f0a841354151b85fde78a9f73318
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

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